3-Nitrophenylboronic Acid → 5-Methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-ylamine

HRID 449223Notes

Reaction equation

HRID 449223 reaction equation
Br[C:2]1[CH:12]=[C:11]([CH3:13])[C:5]2[N:6]=[C:7]([NH2:10])[N:8]=[N:9][C:4]=2[CH:3]=1.[N+:14]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:13][C:11]1[C:5]2[N:6]=[C:7]([NH2:10])[N:8]=[N:9][C:4]=2[CH:3]=[C:2]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[CH:22]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 248227527-Bromo-5-methylbenzo[e][1,2,4]triazin-3-amine

Product 1

HCID 598376075-Methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-ylamineYield 73%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

An oven dried 25 mL round bottom flask was charged with 7-bromo-5-methyl-benzo[1,2,4]triazin-3-ylamine (1.05 g, 4.49 mmol, 1 equiv), 3-Nitro phenyl boronic acid (1.05 g, 6.29 mmol, 1.4 equiv), sodium carbonate (1.9 g, 18 mmol, 4 equiv) and tetrakis(triphenylphosphine) palladium(0) (0.519 g, 0.449 mmol, 0.1 equiv). The reactants were flushed with argon and diluted with ethylene glycol dimethyl ether (6 mL), ethanol (1 mL) and DI water (1 mL). The reaction vessel was outfitted with condenser and refluxed for 2.5 hours. The reaction was cooled to ambient temperature and diluted with water. The resulting precipitate was filtered off, washed thoroughly with water and dried. Brown solids (0.9 g, 73% yield). MS (ESI+): m/z=282.4, LC retention time: 2.77 min.

Workup

  1. customAn oven dried 25 mL round bottom flask
  2. customThe reactants were flushed with argon
  3. additiondiluted with ethylene glycol dimethyl ether (6 mL), ethanol (1 mL) and DI water (1 mL)
  4. customThe reaction vessel was outfitted with condenser
  5. temperaturerefluxed for 2.5 hours
  6. additiondiluted with water
  7. filtrationThe resulting precipitate was filtered off
  8. washwashed thoroughly with water
  9. customdried

Sources & evidence

ORD record
ord-66af02ed9cb94322b70340b4f316b657
Source dataset
uspto-grants-2013_07
Patent number
US08481536B2

Reaction notes

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